4-amino-N-(prop-2-ynyl)benzenesulfonamide | 1092276-39-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-amino-N-(prop-2-ynyl)benzenesulfonamide
• 英文别名: N-propargylsulfanilamide；4-amino-N-prop-2-ynylbenzenesulfonamide
• CAS: 1092276-39-5
• 化学式: C₉H₁₀N₂O₂S
• 分子量: 210.257
• InChiKey: BROQKQRMUUQFGV-UHFFFAOYSA-N

物化性质

• 熔点：
  131-132 °C
• 沸点：
  391.0±52.0 °C(Predicted)
• 密度：
  1.321±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  80.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-amino-N-(prop-2-ynyl)benzenesulfonamide 、 2-叠氮吡啶 在 copper(l) iodide 、 sodium acetate 、 铜 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 16.0h， 以47%的产率得到2-(4-(methylsulfanilamidyl)-1H-1,2,3-triazol-1-yl)pyridine
  参考文献：
  名称：

  CuAAC单击方法用于将二齿金属配合物引入由磺胺衍生的抗生素片段

  摘要：

  为了简化已知的抗生素片段磺胺与二齿吡啶基-三唑口袋的功能，采用了一种简单的“点击化学”方法，从而可以合成钌（II）和rh（I）羰基氯配合物。制备了六种新的复合物并进行了全面表征，包括五种单晶X射线结构，光物理特性和抗微生物活性测试。有趣的是，吡啶环被邻位官能团官能化在二甲基亚砜溶液中，羟甲基导致配体释放速率增加了100倍以上。随后的研究表明，用265 nm的光照射可以进一步加速这一过程。四种配合物的结构表征表明，这是由于羟甲基的空间影响而使Re–N吡啶键延长和减弱的结果（平均（L tri）= 2.19Åvs L tri OH = 2.25Å）团体。尽管存在磺酰胺部分，但有机金属rh（I）吡啶基-三唑官能团仍保持其特征性的荧光性质。其中两种化合物显示出对耐甲氧西林的适度抗菌活性金黄色葡萄球菌，而仅在结构上相似的磺胺甲恶唑在相同条件下无活性。

  DOI：

  10.1021/acs.inorgchem.9b01186
• 作为产物：
  描述：

  4-acetamido-N-(prop-2-ynyl)benzenesulfonamide 在 盐酸 、 水 作用下， 以 乙醇 为溶剂， 以92%的产率得到4-amino-N-(prop-2-ynyl)benzenesulfonamide
  参考文献：
  名称：

  Synthesis of novel sulfanilamide-derived 1,2,3-triazoles and their evaluation for antibacterial and antifungal activities

  摘要：

  A series of novel sulfanilamide-derived 1,2,3-triazole compounds were synthesized in excellent yields via 1,3-dipolar cycloaddition and confirmed by MS. IR and NMR spectra as well as elemental analyses. All the compounds were screened in vitro for their antibacterial and antifungal activities Preliminary results indicated that some target compounds exhibited promising antibacterial potency Especially, 4-amino-N-((1-dodecyl-1H-1,2,3-triazol-4-yl)methyl) benzenesulfonamide. N-((1-(2,4-dichlorobenzyl)- 1H-1,2,3-triazol-4-yl)methyl)-4-aminobenzenesulfonamide and 4-amino-N-((1-(2,4-difluorobenzyl)- 1H-1,2,3-triazol-4-yl)methyl) benzenesulfonamide were found to be the most potent compounds against all the tested strains except for Candida albicans (ATCC76615) and Candida mycoderma. (C) 2010 Elsevier Masson SAS All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.07.031

文献信息

• [EN] NOVEL KINASE INHIBITORS<br/>[FR] NOUVEAUX INHIBITEURS DE KINASES
  申请人：ORIGENIS GMBH

  公开号：WO2014060113A1

  公开（公告）日：2014-04-24

  The present invention relates to novel compounds of formula (I) that are capable of inhibiting one or more kinases, especially SYK (Spleen Tyrosine Kinase), LRRK2 (Leucine-rich repeat kinase 2) and/or MYLK (Myosin light chain kinase) or mutants thereof. The compounds find applications in the treatment of a variety of diseases. These diseases include autoimmune diseases, inflammatory diseases, bone diseases, metabolic diseases, neurological and neurodegenerative diseases, cancer, cardiovascular diseases, allergies, asthma, alzheimer's disease, parkinson's disease, skin disorders, eye diseases, infectious diseases and hormone-related diseases.

  本发明涉及一种具有公式（I）的新化合物，能够抑制一个或多个激酶，特别是SYK（脾酪氨酸激酶）、LRRK2（富含亮氨酸重复的激酶2）和/或MYLK（肌球蛋白轻链激酶）或其突变体。这些化合物在治疗多种疾病中发挥作用。这些疾病包括自身免疫疾病、炎症性疾病、骨疾病、代谢性疾病、神经和神经退行性疾病、癌症、心血管疾病、过敏、哮喘、阿尔茨海默病、帕金森病、皮肤疾病、眼部疾病、传染病和激素相关疾病。
• [EN] PYRAZOLO[4,3-D]PYRIMIDINES AS KINASE INHIBITORS<br/>[FR] PYRAZOLO[4,3-D]PYRIMIDINES UTILES EN TANT QU'INHIBITEURS DE KINASES
  申请人：ORIGENIS GMBH

  公开号：WO2014060112A1

  公开（公告）日：2014-04-24

  The present invention relates to novel compounds of formula (I) that are capable of inhibiting one or more kinases, especially SYK (Spleen Tyrosine Kinase), LRRK2 (Leucine-rich repeat kinase 2) and/or MYLK (Myosin light chain kinase) or mutants thereof. The compounds find applications in the treatment of a variety of diseases. These diseases include autoimmune diseases, inflammatory diseases, bone diseases, metabolic diseases, neurological and neurodegenerative diseases, cancer, cardiovascular diseases, allergies, asthma, alzheimer's disease, parkinson's disease, skin disorders, eye diseases, infectious diseases and hormone-related diseases.

  本发明涉及具有式（I）的新化合物，其能够抑制一个或多个激酶，特别是SYK（脾酪氨酸激酶）、LRRK2（富含亮氨酸重复的激酶2）和/或MYLK（肌球蛋白轻链激酶）或其突变体。这些化合物可用于治疗多种疾病。这些疾病包括自身免疫疾病、炎症性疾病、骨疾病、代谢性疾病、神经和神经退行性疾病、癌症、心血管疾病、过敏、哮喘、阿尔茨海默病、帕金森病、皮肤疾病、眼部疾病、传染病和激素相关疾病。
• Synthesis and antimicrobial evaluation of sulfanilamide- and carbohydrate-derived 1,4-disubstitued-1,2,3-triazoles via click chemistry
  作者：Kadir Ay、Beyza Ispartaloğlu、Erkan Halay、Emriye Ay、İhsan Yaşa、Tamer Karayıldırım

  DOI：10.1007/s00044-017-1864-3

  日期：2017.7

  including d-glucose, d-galactose, d-mannose, and d-fructose were synthesized in good yields from azidosugars with propargyl sulfanilamides using copper catalyst 1,3-dipolar cycloaddition reaction (CuAAC). The structures of new compounds were elucidated by liquid chromatography-mass spectrometry, infrared, one-dimensional- and two-dimensional-nuclear magnetic resonance techniques. All of the new compounds were

  4-取代的Sulfanilamido-1,2,3-三唑与单糖（共轭8 - 17），包括d -葡萄糖，ð半乳糖，ð甘露糖，和d -fructose使用铜催化剂在从与炔丙基磺胺azidosugars良好的收率合成1,3-偶极环加成反应（CuAAC）。通过液相色谱-质谱，红外，一维和二维核磁共振技术阐明了新化合物的结构。所有这些新化合物均经过体外抗金黄色葡萄球菌，枯草芽孢杆菌，大肠杆菌，鼠伤寒沙门氏菌，肺炎克雷伯菌，粪肠球菌，铜绿假单胞菌和白色念珠菌具有抗菌和抗真菌活性。实验结果表明，对测试微生物的最低抑菌浓度范围为0.078至5.0 mg / mL，具有抗菌活性。
• NOVEL KINASE INHIBITORS
  申请人：ORIGENIS GMBH

  公开号：US20150259340A1

  公开（公告）日：2015-09-17

  The present invention relates to novel compounds of formula (I) that are capable of inhibiting one or more kinases, especially SYK (Spleen Tyrosine Kinase), LRRK2 (Leucine-rich repeat kinase 2) and/or MYLK (Myosin light chain kinase) or mutants thereof. The compounds find applications in the treatment of a variety of diseases. These diseases include autoimmune diseases, inflammatory diseases, bone diseases, metabolic diseases, neurological and neurodegenerative diseases, cancer, cardiovascular diseases, allergies, asthma, alzheimer's disease, parkinson's disease, skin disorders, eye diseases, infectious diseases and hormone-related diseases.

  本发明涉及式（I）的新型化合物，能够抑制一个或多个激酶，特别是SYK（脾酪氨酸激酶）、LRRK2（富含亮氨酸重复的激酶2）和/或MYLK（肌球蛋白轻链激酶）或其突变体。这些化合物可用于治疗各种疾病。这些疾病包括自身免疫性疾病、炎症性疾病、骨病、代谢性疾病、神经和神经退行性疾病、癌症、心血管疾病、过敏、哮喘、阿尔茨海默病、帕金森病、皮肤疾病、眼部疾病、传染病和与激素相关的疾病。
• PYRAZOLO[4,3-D]PYRIMIDINES AS KINASE INHIBITORS
  申请人：ORIGENIS GMBH

  公开号：US20150266882A1

  公开（公告）日：2015-09-24

  The present invention relates to novel compounds of formula (I) that are capable of inhibiting one or more kinases, especially SYK (Spleen Tyrosine Kinase), LRRK2 (Leucine-rich repeat kinase 2) and/or MYLK (Myosin light chain kinase) or mutants thereof. The compounds find applications in the treatment of a variety of diseases. These diseases include autoimmune diseases, inflammatory diseases, bone diseases, metabolic diseases, neurological and neurodegenerative diseases, cancer, cardiovascular diseases, allergies, asthma, alzheimer's disease, parkinson's disease, skin disorders, eye diseases, infectious diseases and hormone-related diseases.

  本发明涉及化合物(I)的新型化合物，能够抑制一个或多个激酶，特别是SYK（脾酪氨酸激酶）、LRRK2（富含亮氨酸重复的激酶2）和/或MYLK（肌球蛋白轻链激酶）或其突变体。这些化合物在治疗多种疾病方面有应用。这些疾病包括自身免疫疾病、炎症性疾病、骨病、代谢性疾病、神经和神经退行性疾病、癌症、心血管疾病、过敏、哮喘、阿尔茨海默病、帕金森病、皮肤疾病、眼病、传染病和激素相关疾病。